Carbon tetrabromide → 1-[(2E)-6-bromo-4-(4-chlorophenyl)-2,3-difluoro-2-hexenyl]-3-phenoxybenzene
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](/[C:12](/[F:29])=[C:13](\[F:28])/[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)[CH2:9][CH2:10]O)=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC>[Br:31][CH2:10][CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)/[C:12](/[F:29])=[C:13](\[F:28])/[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of (4E)-3-(4-chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexen-1-ol (0.10 g, 0.24 mmol) in ether (5 ml) under nitrogen was added carbon tetrabromide (0.085 g, 0.256 mmol), followed by triphenylphosphine (0.067 g, 0.255 mmol), and the resulting mixture was stirred overnight at room temperature. Additional quantities of carbon tetrabromide (0.17 g, 0.51 mmol) and triphenylphosphine (0.134 g, 0.51 mmol) were added, and the reaction mixture was stirred for five hours. The reaction mixture was concentrated in vacuo and the residue chromatographed on preparative thin layer silica gel plates, developing with methylene chloride to afford the title compound as a colorless oil (0.08 g) which was characterized by 1MMR, 19FNMR and mass spectral analysis.
Workup
- stirringthe reaction mixture was stirred for five hours
- concentrationThe reaction mixture was concentrated in vacuo
- customthe residue chromatographed on preparative thin layer silica gel plates
Sources & evidence
- ORD record
- ord-9dbeb36388cb4ae5850df4da9ed1a482
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06506800B2
Reaction notes
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